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Synthesis method of N-{2-[4-(2-pyrimidyl)-1-piperazine}adamantine-1-formide

A synthetic method, pyrimidine-based technology, applied in the direction of organic chemistry, can solve the problems of increasing the concentration of serotonin, slow onset of action, etc., and achieve the effect of simple route, easy operation, and sufficient source of raw materials

Inactive Publication Date: 2011-09-14
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Traditional antidepressants are monoamine oxidase inhibitors, which generally have the defect of slow onset of action. Studies have found that pyrimidinyl piperazine derivatives have a strong affinity for 5-hydroxytryptamine, which can increase the concentration of 5-hydroxytryptamine in the neural space of the brain. Play an antidepressant effect, take effect quickly, overcome the hysteresis effect of traditional drugs, and is a new type of antidepressant drug (Xu Juan, Wang Lin, Chinese Journal of Medicinal Chemistry, 2003, 6, 367)

Method used

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  • Synthesis method of N-{2-[4-(2-pyrimidyl)-1-piperazine}adamantine-1-formide
  • Synthesis method of N-{2-[4-(2-pyrimidyl)-1-piperazine}adamantine-1-formide

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Embodiment 1

[0024] 1, the synthesis of 1-(2-pyrimidine) piperazine hydrochloride

[0025] In a 100mL three-necked flask, add 3.01g of 2-chloropyrimidine and 25mL of water, stir and heat to 40°C, add 4.80g of anhydrous piperazine and 3.06g of anhydrous sodium carbonate, react at constant temperature for 4 hours, cool to room temperature, and filter to remove the precipitate , the filtrate was extracted four times with 20mL dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure to a yellow oily liquid, the yellow oily liquid was dissolved in 40mL ether, and dry hydrogen chloride gas was introduced to precipitate white The solid was filtered and dried to obtain 4.85 g of 1-(2-pyrimidine)piperazine hydrochloride as a white solid with a yield of 92% and a melting point of 283-285°C.

[0026] 2. Synthesis of N-{2-[4-(2-pyrimidinyl)-1-piperazine]ethyl}phthalimide

[0027] In a 100mL beaker, add 5.6g of 1-(2-pyrimi...

Embodiment 2

[0034] 1, the synthesis of 1-(2-pyrimidine) piperazine hydrochloride

[0035] In a 100mL three-necked flask, add 3.01g of 2-chloropyrimidine and 40mL of water, stir and heat to 60°C, add 5.80g of anhydrous piperazine and 3.06g of anhydrous sodium carbonate in batches, react at constant temperature for 3 hours, and cool to room temperature , filtered to remove the precipitate, the filtrate was extracted four times with 20mL dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure to a yellow oily liquid, the yellow oily liquid was dissolved in 40mL ether, and passed into a dry Hydrogen chloride gas, a white solid was precipitated, filtered, and dried to obtain 4.58 g of a white solid of 1-(2-pyrimidine)piperazine hydrochloride, with a yield of 87% and a melting point of 283-285°C.

[0036] 2. Synthesis of N-{2-[4-(2-pyrimidinyl)-1-piperazine]ethyl}phthalimide

[0037]In a 100mL beaker, add 5.6g of ...

Embodiment 3

[0044] 1, the synthesis of 1-(2-pyrimidine) piperazine hydrochloride

[0045] In a 100mL three-necked flask, add 3.01g of 2-chloropyrimidine and 50mL of water, stir and heat to 80°C, add 7.80g of anhydrous piperazine and 3.06g of anhydrous sodium carbonate in batches, react at constant temperature for 1h, and cool to room temperature , filtered to remove the precipitate, the filtrate was extracted four times with 20mL dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure to a yellow oily liquid, the yellow oily liquid was dissolved in 40mL ether, and passed into a dry Hydrogen chloride gas precipitated a white solid, filtered and dried to obtain 4.22 g of 1-(2-pyrimidine)piperazine hydrochloride as a white solid with a yield of 80.1% and a melting point of 283-285°C.

[0046] 2. Synthesis of N-{2-[4-(2-pyrimidinyl)-1-piperazine]ethyl}phthalimide

[0047] In a 100mL beaker, add 5.6g of 1-(2-pyri...

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Abstract

The invention discloses a synthesis method of N-{2-[4-(2-pyrimidyl)-1-piperazine} adamantane-1-formide. The structural formula of the N-{2-[4-(2-pyrimidyl)-1-piperazine} adamantine-1-formide is shown in the specification. In the synthesis method, based on 2-chloropyrimidine as a main raw material, an adamantine-containing antidepressant N-{2-[4-(2-pyrimidyl)-1-piperazine} adamantane-1-formide is synthesized through nitrogen alkylation of 2-chloropyrimidine and anhydrous piperazine, alkylation of another nitrogen atom on the piperazine and bromohydrocarbon, Gabriel hydrazinolysis and amidation. The synthesis route in the invention is simple and practicable, raw material sources are abundant, reaction steps are less, and the yield of the product is high.

Description

technical field [0001] The invention relates to a synthesis method of N-{2-[4-(2-pyrimidinyl)-1-piperazine]ethyl}adamantane-1-carboxamide. Background technique [0002] Adamantane is a highly symmetrical, cage-like alkane with the chemical formula C 10 h 16 . Non-toxic, tasteless, odorless, lipophilic, easy to generate derivatives. More and more new drugs containing adamantyl groups are constantly appearing, and the synthesis and clinical pharmacological research of adamantane-type specific drugs at home and abroad are constantly being reported, and adamantane-type drugs have also become one of the hot spots in drug synthesis research (Lamoureux. G; Artavia, G. J. Curr. Med. Chem. 2010, 17, 2967). [0003] Traditional antidepressants are monoamine oxidase inhibitors, which generally have the defect of slow onset of action. Studies have found that pyrimidinyl piperazine derivatives have a strong affinity for 5-hydroxytryptamine, which can increase the concentration of 5-h...

Claims

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Application Information

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IPC IPC(8): C07D403/04
Inventor 郭建维苏强杨楚芬彭进平崔亦华
Owner GUANGDONG UNIV OF TECH
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